diff --git a/CHANGELOG.txt b/CHANGELOG.txt
index 738faed172..d36e7d7fea 100644
--- a/CHANGELOG.txt
+++ b/CHANGELOG.txt
@@ -37,6 +37,7 @@ Changelog
  * Move translations in `nl_NL` to `nl` (Loïc Teixeira, Coen van der Kamp)
  * Add documentation for how to redirect to a separate page on Form builder submissions using ``RoutablePageMixin`` (Nick Smith)
  * Refactored index listing views and made column sort-by headings more consistent (Matt Westcott)
+ * Added the ability to customise the pre-filled Image title on upload and it now defaults to the filename without the file extension (LB Johnston)
  * Fix: Delete button is now correct colour on snippets and modeladmin listings (Brandon Murch)
  * Fix: Ensure that StreamBlock / ListBlock-level validation errors are counted towards error counts (Matt Westcott)
  * Fix: InlinePanel add button is now keyboard navigatable (Jesse Menn)
diff --git a/docs/advanced_topics/images/index.rst b/docs/advanced_topics/images/index.rst
index 8876ac7ed7..5633d2ae0c 100644
--- a/docs/advanced_topics/images/index.rst
+++ b/docs/advanced_topics/images/index.rst
@@ -13,3 +13,4 @@ Images
     feature_detection
     image_serve_view
     focal_points
+    title_generation_on_upload
diff --git a/docs/advanced_topics/images/title_generation_on_upload.md b/docs/advanced_topics/images/title_generation_on_upload.md
new file mode 100644
index 0000000000..ad2affba60
--- /dev/null
+++ b/docs/advanced_topics/images/title_generation_on_upload.md
@@ -0,0 +1,108 @@
+# Title generation on upload
+
+Override how the title is set when adding a single image, multiple images or uploading an image within a chooser modal.
+
+When a file is dropped into the multi-upload page or selected on the single file selection form a title will be automatically populated into the Title field. The default behaviour is to use the image's filename excluding the extension.
+
+You can customise the resolved value of this title using a JavaScript [event listener](https://developer.mozilla.org/en-US/docs/Web/API/EventTarget/addEventListener) which will listen to the `'wagtail:images-upload'` event.
+
+The simplest way to add JavaScript to the editor is via the [`insert_global_admin_js` hook](../../reference/hooks.html#insert-global-admin-js), however any JavaScript that adds the event listener will work.
+
+## DOM Event
+
+The event name to listen for is `'wagtail:images-upload'`. It will be dispatched on the image upload `form`. The event's `detail` attribute will contain:
+
+-   `data` - An object which includes the `title` to be used. It is the filename with the extension removed.
+-   `maxTitleLength` - An integer (or `null`) which is the maximum length of the `Image` model title field.
+-   `filename` - The original filename without the extension removed.
+
+To modify the generated `Image` title, access and update `event.detail.data.title`, no return value is needed.
+
+For single image uploads, the custom event will only run if the title does not already have a value so that we do not overwrite whatever the user has typed.
+
+You can prevent the default behaviour by calling `event.preventDefault()`. For the single upload page or modals, this will not pre-fill any value into the title. For multiple upload, this will avoid any title submission and use the filename title only (with file extension) as a title is required to save the image.
+
+The event will 'bubble' up so that you can simply add a global `document` listener to capture all of these events, or you can scope your listener or handler logic as needed to ensure you only adjust titles in some specific scenarios.
+
+See MDN for more information about [custom JavasScript events](https://developer.mozilla.org/en-US/docs/Web/Events/Creating_and_triggering_events).
+
+## Code Examples
+
+### Removing any url unsafe characters from the title
+
+```python
+# wagtail_hooks.py
+from django.utils.safestring import mark_safe
+
+from wagtail.core import hooks
+
+
+@hooks.register("insert_global_admin_js")
+def get_global_admin_js():
+    return mark_safe(
+    """
+    <script>
+    window.addEventListener('DOMContentLoaded', function () {
+        document.addEventListener('wagtail:images-upload', function(event) {
+            var newTitle = (event.detail.data.title || '').replace(/[^a-zA-Z0-9\s-]/g, "");
+            event.detail.data.title = newTitle;
+        });
+    });
+    </script>
+    """
+    )
+```
+
+### Changing generated titles on the page editor only to remove dashes/underscores
+
+Using the [`insert_editor_js` hook](../../reference/hooks.html#insert-editor-js) instead so that this script will not run on the `Image` upload page, only on page editors.
+
+```python
+# wagtail_hooks.py
+from django.utils.safestring import mark_safe
+
+from wagtail.core import hooks
+
+
+@hooks.register("insert_editor_js")
+def get_global_admin_js():
+    return mark_safe(
+    """
+    <script>
+    window.addEventListener('DOMContentLoaded', function () {
+        document.addEventListener('wagtail:images-upload', function(event) {
+            // replace dashes/underscores with a space
+            var newTitle = (event.detail.data.title || '').replace(/(\s|_|-)/g, " ");
+            event.detail.data.title = newTitle;
+        });
+    });
+    </script>
+    """
+    )
+```
+
+### Stopping pre-filling of title based on filename
+
+```python
+# wagtail_hooks.py
+from django.utils.safestring import mark_safe
+
+from wagtail.core import hooks
+
+
+@hooks.register("insert_global_admin_js")
+def get_global_admin_js():
+    return mark_safe(
+    """
+    <script>
+    window.addEventListener('DOMContentLoaded', function () {
+        document.addEventListener('wagtail:images-upload', function(event) {
+            // will stop title pre-fill on single file uploads
+            // will set the multiple upload title to the filename (with extension)
+            event.preventDefault();
+        });
+    });
+    </script>
+    """
+    )
+```
diff --git a/docs/releases/2.15.rst b/docs/releases/2.15.rst
index 1d5e071490..cdf1dc7c1c 100644
--- a/docs/releases/2.15.rst
+++ b/docs/releases/2.15.rst
@@ -53,6 +53,7 @@ Other features
  * Translations in ``nl_NL`` are moved to the ``nl`` po files. ``nl_NL`` translation files are deleted. Projects that use ``LANGUAGE_CODE = 'nl-nl'`` will automatically fallback to ``nl``. (Loïc Teixeira, Coen van der Kamp)
  * Add documentation for how to redirect to a separate page on Form builder submissions using ``RoutablePageMixin`` (Nick Smith)
  * Refactored index listing views and made column sort-by headings more consistent (Matt Westcott)
+ * Added the ability to customise the pre-filled Image title on upload and it now defaults to the filename without the file extension (LB Johnston)
 
 Bug fixes
 ~~~~~~~~~
diff --git a/wagtail/admin/views/generic/multiple_upload.py b/wagtail/admin/views/generic/multiple_upload.py
index f81837e04f..e33c391a87 100644
--- a/wagtail/admin/views/generic/multiple_upload.py
+++ b/wagtail/admin/views/generic/multiple_upload.py
@@ -125,7 +125,7 @@ class AddView(PermissionCheckedMixin, TemplateView):
         # Build a form for validation
         upload_form_class = self.get_upload_form_class()
         form = upload_form_class({
-            'title': request.FILES['files[]'].name,
+            'title': request.POST.get('title', request.FILES['files[]'].name),
             'collection': request.POST.get('collection'),
         }, {
             'file': request.FILES['files[]'],
diff --git a/wagtail/images/static_src/wagtailimages/js/add-multiple.js b/wagtail/images/static_src/wagtailimages/js/add-multiple.js
index 183b0f89ff..c9825fbf8b 100644
--- a/wagtail/images/static_src/wagtailimages/js/add-multiple.js
+++ b/wagtail/images/static_src/wagtailimages/js/add-multiple.js
@@ -97,6 +97,35 @@ $(function() {
             }
         },
 
+        /**
+         * Allow a custom title to be defined by an event handler for this form.
+         * If event.preventDefault is called, the original behaviour of using the raw
+         * filename (with extension) as the title is preserved.
+         *
+         * @example
+         * document.addEventListener('wagtail:images-upload', function(event) {
+         *   // remove file extension
+         *   var newTitle = (event.detail.data.title || '').replace(/\.[^\.]+$/, "");
+         *   event.detail.data.title = newTitle;
+         * });
+         *
+         * @param {HtmlElement[]} form
+         * @returns {{name: 'string', value: *}[]}
+         */
+        formData: function(form) {
+            var filename = this.files[0].name;
+            var data = { title: filename.replace(/\.[^\.]+$/, '') };
+            var maxTitleLength = window.fileupload_opts.max_title_length;
+
+            var event = form.get(0).dispatchEvent(new CustomEvent(
+                'wagtail:images-upload',
+                { bubbles: true, cancelable: true, detail: { data: data, filename: filename, maxTitleLength: maxTitleLength } }
+            ));
+
+            // default behaviour (title is just file name)
+            return event ? form.serializeArray().concat({ name:'title', value: data.title }) : form.serializeArray();
+        },
+
         done: function(e, data) {
             var itemElement = $(data.context);
             var response = JSON.parse(data.result);
diff --git a/wagtail/images/static_src/wagtailimages/js/image-chooser-modal.js b/wagtail/images/static_src/wagtailimages/js/image-chooser-modal.js
index 8b46c3f4b3..cdc47ec0c8 100644
--- a/wagtail/images/static_src/wagtailimages/js/image-chooser-modal.js
+++ b/wagtail/images/static_src/wagtailimages/js/image-chooser-modal.js
@@ -34,11 +34,26 @@ function ajaxifyImageUploadForm(modal) {
     fileWidget.on('change', function () {
         var titleWidget = $('#id_image-chooser-upload-title', modal.body);
         var title = titleWidget.val();
+        // do not override a title that already exists (from manual editing or previous upload)
         if (title === '') {
             // The file widget value example: `C:\fakepath\image.jpg`
             var parts = fileWidget.val().split('\\');
-            var fileName = parts[parts.length - 1];
-            titleWidget.val(fileName);
+            var filename = parts[parts.length - 1];
+
+            // allow event handler to override filename (used for title) & provide maxLength as int to event
+            var maxTitleLength = parseInt(titleWidget.attr('maxLength') || '0', 10) || null;
+            var data = { title: filename.replace(/\.[^\.]+$/, '') };
+
+            // allow an event handler to customise data or call event.preventDefault to stop any title pre-filling
+            var form = fileWidget.closest('form').get(0);
+            var event = form.dispatchEvent(new CustomEvent(
+                'wagtail:images-upload',
+                { bubbles: true, cancelable: true, detail: { data: data, filename: filename, maxTitleLength: maxTitleLength } }
+            ));
+
+            if (!event) return; // do not set a title if event.preventDefault(); is called by handler
+
+            titleWidget.val(data.title);
         }
     });
 }
diff --git a/wagtail/images/templates/wagtailimages/images/add.html b/wagtail/images/templates/wagtailimages/images/add.html
index 849048d391..c88d35a71a 100644
--- a/wagtail/images/templates/wagtailimages/images/add.html
+++ b/wagtail/images/templates/wagtailimages/images/add.html
@@ -11,6 +11,31 @@
     {% url 'wagtailadmin_tag_autocomplete' as autocomplete_url %}
     <script>
         $(function() {
+            $('#id_file').on(
+                'change',
+                function() {
+                    var $titleField = $('#id_title');
+
+                    // do not override a title that already exists (from manual editing or previous upload)
+                    if ($titleField.val()) return;
+
+                    // file widget value example: `C:\fakepath\image.jpg` - convert to just the filename part
+                    var filename = $(this).val().split('\\').slice(-1)[0];
+                    var data = { title: filename.replace(/\.[^\.]+$/, '') };
+                    var maxTitleLength = parseInt($titleField.attr('maxLength') || '0', 10) || null;
+
+                    // allow an event handler to customise data or call event.preventDefault to stop any title pre-filling
+                    var form = $(this).closest('form').get(0);
+                    var event = form.dispatchEvent(new CustomEvent(
+                        'wagtail:images-upload',
+                        { bubbles: true, cancelable: true, detail: { data: data, filename: filename, maxTitleLength: maxTitleLength } }
+                    ));
+
+                    if (!event) return; // do not set a title if event.preventDefault(); is called by handler
+
+                    $titleField.val(data.title);
+                }
+            );
             $('#id_tags').tagit({
                 autocomplete: {source: "{{ autocomplete_url|addslashes }}"}
             });
diff --git a/wagtail/images/templates/wagtailimages/multiple/add.html b/wagtail/images/templates/wagtailimages/multiple/add.html
index f51c06fc66..719de2cfa6 100644
--- a/wagtail/images/templates/wagtailimages/multiple/add.html
+++ b/wagtail/images/templates/wagtailimages/multiple/add.html
@@ -106,6 +106,7 @@
             simple_upload_url: "{% url 'wagtailimages:add' %}",
             accepted_file_types: /\.({{ allowed_extensions|join:"|" }})$/i, //must be regex
             max_file_size: {{ max_filesize|stringformat:"s"|default:"null" }}, //numeric format
+            max_title_length: {{ max_title_length|stringformat:"s"|default:"null" }}, //numeric format
             errormessages: {
                 max_file_size: "{{ error_max_file_size|escapejs }}",
                 accepted_file_types: "{{ error_accepted_file_types|escapejs }}"
diff --git a/wagtail/images/tests/test_admin_views.py b/wagtail/images/tests/test_admin_views.py
index 3a5d0e63b0..07190dde6f 100644
--- a/wagtail/images/tests/test_admin_views.py
+++ b/wagtail/images/tests/test_admin_views.py
@@ -13,6 +13,7 @@ from django.utils.safestring import mark_safe
 
 from wagtail.admin.admin_url_finder import AdminURLFinder
 from wagtail.core.models import Collection, GroupCollectionPermission, get_root_collection_id
+from wagtail.images import get_image_model
 from wagtail.images.models import UploadedImage
 from wagtail.images.utils import generate_signature
 from wagtail.tests.testapp.models import CustomImage, CustomImageWithAuthor
@@ -1376,6 +1377,7 @@ class TestMultipleImageUploader(TestCase, WagtailTestUtils):
         This tests that a POST request to the add view saves the image and returns an edit form
         """
         response = self.client.post(reverse('wagtailimages:add_multiple'), {
+            'title': 'test title',
             'files[]': SimpleUploadedFile('test.png', get_test_image_file().file.getvalue()),
         })
 
@@ -1386,21 +1388,59 @@ class TestMultipleImageUploader(TestCase, WagtailTestUtils):
 
         # Check image
         self.assertIn('image', response.context)
-        self.assertEqual(response.context['image'].title, 'test.png')
+        self.assertEqual(response.context['image'].title, 'test title')
         self.assertTrue(response.context['image'].file_size)
         self.assertTrue(response.context['image'].file_hash)
 
+        # Check image title
+        image = get_image_model().objects.get(title='test title')
+        self.assertNotIn('title', image.filename)
+        self.assertIn('.png', image.filename)
+
         # Check form
         self.assertIn('form', response.context)
-        self.assertEqual(response.context['form'].initial['title'], 'test.png')
         self.assertEqual(response.context['edit_action'], '/admin/images/multiple/%d/' % response.context['image'].id)
         self.assertEqual(response.context['delete_action'], '/admin/images/multiple/%d/delete/' % response.context['image'].id)
+        self.assertEqual(response.context['form'].initial['title'], 'test title')
+
+        # Check JSON
+        response_json = json.loads(response.content.decode())
+        self.assertIn('form', response_json)
+        self.assertIn('image_id', response_json)
+        self.assertIn('success', response_json)
+        self.assertEqual(response_json['image_id'], response.context['image'].id)
+        self.assertTrue(response_json['success'])
+
+    def test_add_post_no_title(self):
+        """
+        A POST request to the add view without the title value saves the image and uses file title if needed
+        """
+        response = self.client.post(reverse('wagtailimages:add_multiple'), {
+            'files[]': SimpleUploadedFile('no-title.png', get_test_image_file().file.getvalue()),
+        }, HTTP_X_REQUESTED_WITH='XMLHttpRequest')
+
+        # Check response
+        self.assertEqual(response.status_code, 200)
+        self.assertEqual(response['Content-Type'], 'application/json')
+
+        # Check image
+        self.assertIn('image', response.context)
+        self.assertTrue(response.context['image'].file_size)
+        self.assertTrue(response.context['image'].file_hash)
+
+        # Check image title
+        image = get_image_model().objects.get(title='no-title.png')
+        self.assertEqual('no-title.png', image.filename)
+        self.assertIn('.png', image.filename)
+
+        # Check form
+        self.assertIn('form', response.context)
+        self.assertEqual(response.context['form'].initial['title'], 'no-title.png')
 
         # Check JSON
         response_json = json.loads(response.content.decode())
         self.assertIn('form', response_json)
         self.assertIn('success', response_json)
-        self.assertTrue(response_json['success'])
 
     def test_add_post_nofile(self):
         """
diff --git a/wagtail/images/views/multiple.py b/wagtail/images/views/multiple.py
index 8599ceece2..4a7c88147a 100644
--- a/wagtail/images/views/multiple.py
+++ b/wagtail/images/views/multiple.py
@@ -55,6 +55,7 @@ class AddView(BaseAddView):
 
         context.update({
             'max_filesize': self.form.fields['file'].max_upload_size,
+            'max_title_length': self.form.fields['title'].max_length,
             'allowed_extensions': ALLOWED_EXTENSIONS,
             'error_max_file_size': self.form.fields['file'].error_messages['file_too_large_unknown_size'],
             'error_accepted_file_types': self.form.fields['file'].error_messages['invalid_image_extension'],